2-[2-[3-Bromo-8-(4-morpholinyl)imidazo[1,2-b]pyridazin-2-yl]ethyl]quinoline → 1-Methyl-3-[4-[8-(morpholin-4-yl)-2-[2-(quinolin-2-yl)ethyl]imidazo[1,2-b]pyridazin-3-yl]phenyl]-4-[[2-(trimethylsilyl)ethoxy]methyl]-4,5-dihydro-1H-1,2,4-triazol-5-one

HRID 718647Notes

Reaction equation

Br[C:2]1[N:6]2[N:7]=[CH:8][CH:9]=[C:10]([N:11]3[CH2:16][CH2:15][O:14][CH2:13][CH2:12]3)[C:5]2=[N:4][C:3]=1[CH2:17][CH2:18][C:19]1[CH:28]=[CH:27][C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20]=1.[CH3:29][N:30]1[C:34](=[O:35])[N:33]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:42])[CH3:41])[C:32]([C:44]2[CH:49]=[CH:48][C:47](B3OC(C)(C)C(C)(C)O3)=[CH:46][CH:45]=2)=[N:31]1>>[CH3:29][N:30]1[C:34](=[O:35])[N:33]([CH2:36][O:37][CH2:38][CH2:39][Si:40]([CH3:43])([CH3:41])[CH3:42])[C:32]([C:44]2[CH:45]=[CH:46][C:47]([C:2]3[N:6]4[N:7]=[CH:8][CH:9]=[C:10]([N:11]5[CH2:16][CH2:15][O:14][CH2:13][CH2:12]5)[C:5]4=[N:4][C:3]=3[CH2:17][CH2:18][C:19]3[CH:28]=[CH:27][C:26]4[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:20]=3)=[CH:48][CH:49]=2)=[N:31]1

Participants

Reactant 2

HCID 1177286942-[2-[3-Bromo-8-(4-morpholinyl)imidazo[1,2-b]pyridazin-2-yl]ethyl]quinoline

HCID 1317341771-Methyl-3-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-[[2-(trimethylsilyl)ethoxy]methyl]-4,5-dihydro-1H-1,2,4-triazol-5-one

Product 1

HCID 1239382441-Methyl-3-[4-[8-(morpholin-4-yl)-2-[2-(quinolin-2-yl)ethyl]imidazo[1,2-b]pyridazin-3-yl]phenyl]-4-[[2-(trimethylsilyl)ethoxy]methyl]-4,5-dihydro-1H-1,2,4-triazol-5-one

Procedure

Compound 46a was subjected to Suzuki coupling conditions with compound 51d as described in Example 38, Step A to obtain compound 51e as a light yellow solid. Mass Spectrum (LCMS, ESI pos.): Calcd. for C36H42N8O3Si: 663.3 (M+H). Found: 663.4.

Sources & evidence

ORD record: ord-9304abbbab7c4374aa96150b1ff41b35
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193736B2

Reaction notes

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